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Dipyridylphenazinyl red/orange thermally excited delayed fluorescent material, synthesis method and application

A technology of delayed fluorescence and synthesis method, which is applied in the direction of luminescent materials, chemical instruments and methods, compounds of group 5/15 elements of the periodic table, etc., can solve the problems of concentration quenching, low efficiency of light-emitting devices, fast decay, etc., and achieve Improve efficiency, reduce quenching effect, and inhibit the effect of intermolecular interaction

Active Publication Date: 2021-10-15
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to solve the problem of concentration quenching caused by the large molecular polarity of the existing red / orange light TADF materials and the problems of low efficiency and fast decay of electroluminescent devices, and provides a dipyridophenazine-based Red / orange thermally excited delayed fluorescent materials, synthesis methods and applications

Method used

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  • Dipyridylphenazinyl red/orange thermally excited delayed fluorescent material, synthesis method and application
  • Dipyridylphenazinyl red/orange thermally excited delayed fluorescent material, synthesis method and application
  • Dipyridylphenazinyl red/orange thermally excited delayed fluorescent material, synthesis method and application

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specific Embodiment approach 1

[0058] Specific embodiment 1: In this embodiment, the structural formula of the dipyridophenazinyl red / orange photothermal excitation delayed fluorescence material is as follows:

[0059] where X is hydrogen or

[0060] Y is hydrogen,

[0061] Z is hydrogen,

[0062] W is hydrogen or

[0063] When X, Y, Z are hydrogen, W is , its structural formula is:

[0064]

[0065] When X, Y are hydrogen, W, Z are , its structural formula is:

[0066]

[0067] When W, Y, Z are hydrogen, X is , its structural formula is:

[0068]

[0069] When W and Z are hydrogen, X and Y are , its structural formula is:

[0070]

[0071] When X, Y are hydrogen, W is Z is , its structural formula is:

[0072]

[0073] When W and Z are hydrogen, X is Y is , its structural formula is:

[0074]

specific Embodiment approach 2

[0075] Specific embodiment 2: The synthesis method of the dipyridophenazinyl red / orange photothermal excitation delayed fluorescent material described in specific embodiment 1 is carried out according to the following steps:

[0076] 1. Mix 1 mmol of 5-bromobenzothiadiazole or 4-bromobenzothiadiazole, 1 mmol of triphenylamine-4-boronic acid pinacol ester, 0.05 to 0.1 mmol of tetrakis(triphenylphosphine) palladium, Mix 0.1mmol of tetrabutylammonium bromide, 2-10mmol of sodium hydroxide and 5-10ml of toluene, react at 120°C for 48h, extract with water and dichloromethane, combine the organic layers, remove the organic solvent after drying, and dichloromethane The mixed solvent with petroleum ether is eluent column chromatography purification, obtains 4-(benzo[c][1,2,5]thiadiazol-5-yl)-N,N-diphenylaniline or 4 -(Benzo[c][1,2,5]thiadiazol-4-yl)-N,N-diphenylaniline;

[0077] 2. Add 1 mmol of 5,6-dibromobenzothiadiazole or 4,7-dibromobenzothiadiazole, 2 mmol of triphenylamine-4-bor...

specific Embodiment approach 3

[0082] Specific embodiment three: the difference between this embodiment and specific embodiment two is that in step one, 1 mmol of 5-bromobenzothiadiazole or 4-bromobenzothiadiazole, 1 mmol of triphenylamine-4-boric acid pina Alcohol ester, 0.05mmol of tetrakis(triphenylphosphine) palladium, 0.1mmol of tetrabutylammonium bromide, 6mmol of sodium hydroxide and 10ml of toluene were mixed and reacted at 120°C for 48h; in step 2, 1mmol of 5,6-di Bromobenzothiadiazole or 4,7-dibromobenzothiadiazole, 2mmol of triphenylamine-4-boronic acid pinacol ester, 0.05mmol of tetrakis(triphenylphosphine) palladium, 0.1mmol of tetrabutyl Ammonium bromide, 6mmol sodium hydroxide and 10ml toluene were mixed and reacted at 120°C for 48h. Others are the same as in the second embodiment.

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Abstract

The invention relates to a dipyridophenazinyl red / orange photothermal excitation delayed fluorescent material, a synthesis method and an application thereof, and relates to a fluorescent material, a synthesis method and an application thereof. The invention aims to solve the problems of concentration quenching caused by the large molecular polarity of the existing red / orange light TADF materials and low efficiency and fast decay of electroluminescent devices. The structural formula of this material is as follows: Synthetic method: prepare (6-(4-(diphenylamino)phenyl)benzo[c][1,2,5]thiadiazole-5-yl)diphenylphosphine oxide or (7‑(4‑(diphenylamino)phenyl)benzo[c][1,2,5]thiadiazol‑4‑yl)diphenylphosphine oxide; preparation of desired donor; final product . The material of the invention significantly improves the efficiency of the electroluminescent device, reduces the quenching effect, and enhances the stability of the efficiency of the electroluminescent device. The invention belongs to the field of preparation of fluorescent materials.

Description

technical field [0001] The invention relates to a fluorescent material, a synthesis method and an application thereof. Background technique [0002] It has been more than 20 years since Organic Light-Emitting Diodes (OLED) was first reported. During this period, OLED has achieved rapid development in terms of material synthesis process and device preparation. From light sources used for lighting to mobile phones, digital cameras, and mp3 display screens in our daily life, especially in the field of TV display technology, large-size, transparent, and bendable OLED screens have attracted the attention of countless customers. The singlet excitons generated by electrical excitation account for one quarter, and the triplet excitons account for three quarters. However, the phosphine pair generated by the triplet excitons does not participate in the process of luminescence, so the luminous efficiency of fluorescent OLED devices has been considered to be lower than 25% for a period...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/14C07F9/6561C09K11/06H01L51/50H01L51/54
CPCC07D471/14C07F9/6561C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1044H10K85/6572H10K50/00
Inventor 韩春苗赵炳捷许辉
Owner HEILONGJIANG UNIV
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